Regioselective synthesis of novel dispiro oxindole–pyrrolizine–thiazolidine-2,4-dione hybrids

Asymmetric Construction of Bispiro[oxindole-pyrrolidine-rhodanine]s via Squaramide-Catalyzed Domino Michael/Mannich [3 + 2] Cycloaddition of Rhodanine Derivatives with N-(2,2,2-Trifluoroethyl)isatin Ketimines

“…On the other hand, 2-thioxo-1,3-thiazolidin-4-one, commonly named as rhodanine, has long been sought after by pharmacologists as an important compound in medicinal chemistry . As a peculiar structure with pharmacological activity (Figure ), the modification of rhodanine attracted the attention of chemists . Up to now, only a few cases of asymmetric synthetic methods have been reported for the preparation of chiral thiazolidinone derivatives (Scheme ).…”

Contemporary progress in the green synthesis of spiro-thiazolidines and their medicinal significance: a review

“…R. R. Kumar et al 82 introduced the three-component 1,3-dipolar cycloaddition reaction of isatin ( 68 ), proline ( 70 ), and ( Z )-5-arylidene-3-(2-cyclopropyl-2-oxo-1-phenylethyl)thiazolidine-2,4-diones ( 69 ) gave new dispiro oxindole–pyrrolizine–thiazolidine-2,4-dione derivatives ( 71 ) in opposing to the frequently detected regiochemistry (Scheme 22). These structurally fascinating hybrid heterocycles, including biologically imperative units, served as noteworthy leading compounds.…”

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

“… [382] Reaction performance is enhanced under ultrasonic radiation [383] . L‐Proline 340 and thioproline 342 could be utilized for generation of azomethine yilde and the products could be 341 and 343 respectively [384,385] …”

“…[383] L-Proline 340 and thioproline 342 could be utilized for generation of azomethine yilde and the products could be 341 and 343 respectively. [384,385] A bifunctional cinchona-squaramide organocatalyst 346 was used to catalyze the reaction between 3,5-disubstituted-2,4thiazolidinedione derivatives 344 a-t with 3-isothiocyanato oxindoles 345 a-f under mild conditions to afford a series of oxindole-pyrrolidone-thiazolidinedione bispirocyclic heterocycles 347 a-z containing three contiguous chiral carbons (Scheme 121). These derivatives were obtained with excellent yield (86-99 %), high diastereoselectivities (up to > 99 : 1 dr), and enantioselectivities (up to > 99 % ee).…”